Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Allyl bromide | HCID 7841 | — |
| Reactant | 3-Bromoquinoline | HCID 21413 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 13811728 | HCID 13811728 | — |
Reaction Steps
In an amount of 24.8 mg of copper(I) iodide was added with 9 ml of diethyl ether and 343.5 μl of 3-bromoquinoline, then added dropwise with 1.6 ml of a 1.57 M solution of n-butyllithium in hexane at −78° C., and stirred at −78° C. for 30 minutes. This reaction mixture was added with 71.4 μl of allyl bromide, stirred at −78° C. for 30 minutes, then warmed to 0° C., added with 20 ml of saturated aqueous ammonium chloride, diluted with 20 ml of ethyl acetate, and successively washed twice with 20 ml of saturated aqueous ammonium chloride and once with 20 ml of saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to ethyl acetate/hexane (1:1)) to obtain 130 mg of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07365174B2 |
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| Source dataset | uspto-grants-2008_04 |
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| ORD ID | ord-9f99360e1e224cbb92f42dd0b7c7544e |
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| Source note | uspto-grants-2008_04 |
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